3,3'-[1,2-Phenyl-enebis(methyl-ene)]bis-(1-octylbenzimidazolium) dibromide monohydrate.

In the title hydrated mol-ecular salt, C(38)H(52)N(4) (2+)·2Br(-)·H(2)O, the central benzene ring of the dication makes dihedral angles of 89.47 (13) and 72.69 (12)° with the pendant benzimidazol-3-ium rings. The conformations of the octyl side chains are completely different. In the crystal, the components are linked by O-H⋯Br, C-H⋯Br and C-H⋯O hydrogen bonds into a two-dimensional network lying parallel to the ac plane. Aromatic π-π stacking inter-actions are also observed [shortest centroid-to-centroid separation = 3.5047 (16) Å].

Related literature

For related structures, see: Haque et al. (2012 ▶); Iqbal et al. (2012 ▶); Haque et al. (2011 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C38H52N4 2+·2Br−·H2O

M = 742.67

Triclinic,

a = 8.7203 (4) Å

b = 14.9342 (12) Å

c = 16.4090 (8) Å

α = 115.598 (3)°

β = 104.638 (2)°

γ = 92.358 (3)°

V = 1836.77 (19) Å3

Z = 2

Mo Kα radiation

μ = 2.24 mm−1

T = 100 K

0.42 × 0.32 × 0.24 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.451, T max = 0.614

44354 measured reflections

10659 independent reflections

8816 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.161

S = 1.05

10659 reflections

416 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 2.62 e Å−3

Δρmin = −1.68 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812008331/hb6650sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008331/hb6650Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008331/hb6650Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C38H52N42+·2Br−·H2O	Z = 2
Mr = 742.67	F(000) = 776
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7203 (4) Å	Cell parameters from 9861 reflections
b = 14.9342 (12) Å	θ = 2.5–33.3°
c = 16.4090 (8) Å	µ = 2.24 mm−1
α = 115.598 (3)°	T = 100 K
β = 104.638 (2)°	Block, colourless
γ = 92.358 (3)°	0.42 × 0.32 × 0.24 mm
V = 1836.77 (19) Å3

Bruker SMART APEXII CCD diffractometer	10659 independent reflections
Radiation source: fine-focus sealed tube	8816 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→12
Tmin = 0.451, Tmax = 0.614	k = −20→20
44354 measured reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.1139P)2 + 0.460P] where P = (Fo2 + 2Fc2)/3
10659 reflections	(Δ/σ)max < 0.001
416 parameters	Δρmax = 2.62 e Å−3
0 restraints	Δρmin = −1.68 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Br1	0.86202 (3)	0.228144 (19)	0.215445 (18)	0.01929 (9)
Br2	0.53091 (3)	0.518157 (19)	0.194634 (17)	0.01747 (9)
N1	1.3021 (3)	0.32869 (16)	0.42917 (15)	0.0159 (4)
N2	1.4239 (3)	0.31561 (16)	0.32400 (14)	0.0140 (4)
N3	1.0154 (2)	0.33691 (15)	0.05850 (14)	0.0137 (4)
N4	0.7768 (3)	0.34636 (15)	−0.01797 (14)	0.0136 (4)
C1	1.4628 (3)	0.37063 (18)	0.47927 (17)	0.0150 (5)
C2	1.5453 (3)	0.4119 (2)	0.57555 (18)	0.0198 (5)
H2A	1.4928	0.4172	0.6212	0.024*
C3	1.7092 (4)	0.4446 (2)	0.60039 (18)	0.0215 (5)
H3A	1.7708	0.4731	0.6652	0.026*
C4	1.7875 (3)	0.4373 (2)	0.53320 (19)	0.0201 (5)
H4A	1.9001	0.4607	0.5539	0.024*
C5	1.7050 (3)	0.39691 (19)	0.43801 (18)	0.0173 (5)
H5A	1.7574	0.3923	0.3925	0.021*
C6	1.5401 (3)	0.36325 (18)	0.41248 (16)	0.0138 (4)
C7	1.2832 (3)	0.29643 (19)	0.33687 (18)	0.0157 (5)
H7A	1.1844	0.2646	0.2877	0.019*
C8	1.4578 (3)	0.30028 (19)	0.23524 (16)	0.0157 (5)
H8A	1.5693	0.2873	0.2398	0.019*
H8B	1.4510	0.3631	0.2289	0.019*
C9	1.3448 (3)	0.21446 (18)	0.14737 (16)	0.0139 (4)
C10	1.3942 (3)	0.1203 (2)	0.11448 (18)	0.0183 (5)
H10A	1.4934	0.1124	0.1491	0.022*
C11	1.3001 (3)	0.0386 (2)	0.03209 (19)	0.0205 (5)
H11A	1.3348	−0.0248	0.0105	0.025*
C12	1.1557 (3)	0.04955 (19)	−0.01872 (18)	0.0184 (5)
H12A	1.0908	−0.0065	−0.0750	0.022*
C13	1.1051 (3)	0.14323 (19)	0.01275 (17)	0.0172 (5)
H13A	1.0057	0.1503	−0.0224	0.021*
C14	1.1991 (3)	0.22640 (18)	0.09525 (16)	0.0138 (4)
C15	1.1448 (3)	0.32824 (19)	0.13064 (17)	0.0153 (5)
H15A	1.1069	0.3398	0.1859	0.018*
H15B	1.2381	0.3816	0.1523	0.018*
C16	0.8599 (3)	0.33075 (18)	0.05340 (17)	0.0146 (4)
H16A	0.8150	0.3172	0.0948	0.018*
C17	1.0361 (3)	0.35837 (17)	−0.01316 (16)	0.0134 (4)
C18	1.1739 (3)	0.37683 (19)	−0.03566 (18)	0.0169 (5)
H18A	1.2774	0.3728	−0.0023	0.020*
C19	1.1505 (3)	0.40147 (19)	−0.10989 (18)	0.0184 (5)
H19A	1.2409	0.4149	−0.1278	0.022*
C20	0.9973 (3)	0.40719 (19)	−0.15933 (18)	0.0176 (5)
H20A	0.9874	0.4241	−0.2098	0.021*
C21	0.8599 (3)	0.38897 (18)	−0.13704 (17)	0.0160 (5)
H21A	0.7563	0.3930	−0.1705	0.019*
C22	0.8836 (3)	0.36425 (17)	−0.06195 (17)	0.0134 (4)
C23	1.1749 (3)	0.3223 (2)	0.47208 (19)	0.0192 (5)
H23A	1.0686	0.3131	0.4270	0.023*
H23B	1.1887	0.3865	0.5298	0.023*
C24	1.1778 (4)	0.2361 (2)	0.4980 (2)	0.0234 (6)
H24A	1.2903	0.2349	0.5290	0.028*
H24B	1.1358	0.1715	0.4394	0.028*
C25	1.0773 (4)	0.2460 (2)	0.56425 (19)	0.0210 (5)
H25A	1.1296	0.3050	0.6264	0.025*
H25B	0.9699	0.2586	0.5379	0.025*
C26	1.0565 (4)	0.1530 (2)	0.57879 (19)	0.0216 (5)
H26A	0.9883	0.0966	0.5187	0.026*
H26B	1.1631	0.1337	0.5946	0.026*
C27	0.9807 (4)	0.1681 (2)	0.65654 (19)	0.0222 (5)
H27A	0.8804	0.1954	0.6448	0.027*
H27B	1.0552	0.2187	0.7180	0.027*
C28	0.9415 (3)	0.0714 (2)	0.66330 (18)	0.0199 (5)
H28A	0.8535	0.0253	0.6060	0.024*
H28B	1.0372	0.0380	0.6637	0.024*
C29	0.8916 (4)	0.0871 (2)	0.75032 (19)	0.0229 (5)
H29A	0.7910	0.1156	0.7480	0.028*
H29B	0.9761	0.1364	0.8079	0.028*
C30	0.8650 (4)	−0.0110 (2)	0.7569 (2)	0.0238 (6)
H30A	0.8340	0.0025	0.8140	0.036*
H30B	0.9647	−0.0391	0.7600	0.036*
H30C	0.7793	−0.0594	0.7008	0.036*
C31	0.6030 (3)	0.34999 (19)	−0.04349 (18)	0.0159 (5)
H31A	0.5853	0.4046	−0.0619	0.019*
H31B	0.5656	0.3663	0.0127	0.019*
C32	0.5035 (3)	0.25096 (19)	−0.12457 (18)	0.0177 (5)
H32A	0.5543	0.2282	−0.1761	0.021*
H32B	0.3949	0.2629	−0.1498	0.021*
C33	0.4862 (3)	0.1670 (2)	−0.09634 (19)	0.0215 (5)
H33A	0.4456	0.1920	−0.0406	0.026*
H33B	0.5938	0.1501	−0.0773	0.026*
C34	0.3727 (3)	0.0710 (2)	−0.17547 (19)	0.0219 (5)
H34A	0.3552	0.0241	−0.1494	0.026*
H34B	0.2673	0.0886	−0.1977	0.026*
C35	0.4358 (3)	0.0177 (2)	−0.2595 (2)	0.0230 (5)
H35A	0.5445	0.0044	−0.2365	0.028*
H35B	0.4461	0.0630	−0.2882	0.028*
C36	0.3284 (3)	−0.0821 (2)	−0.3359 (2)	0.0237 (6)
H36A	0.3069	−0.1240	−0.3057	0.028*
H36B	0.2241	−0.0678	−0.3645	0.028*
C37	0.4014 (4)	−0.1421 (2)	−0.4146 (2)	0.0252 (6)
H37A	0.5020	−0.1603	−0.3866	0.030*
H37B	0.3257	−0.2055	−0.4604	0.030*
C38	0.4385 (4)	−0.0865 (3)	−0.4677 (2)	0.0323 (7)
H38A	0.4655	−0.1332	−0.5238	0.048*
H38B	0.5297	−0.0315	−0.4263	0.048*
H38C	0.3441	−0.0587	−0.4872	0.048*
O1W	0.8891 (3)	0.47541 (18)	0.29021 (17)	0.0315 (5)
H1W1	0.877 (5)	0.414 (3)	0.275 (3)	0.043 (12)*
H2W1	0.802 (6)	0.488 (3)	0.267 (3)	0.040 (11)*

	U11	U22	U33	U12	U13	U23
Br1	0.01356 (14)	0.02374 (15)	0.02573 (15)	0.00419 (10)	0.00812 (10)	0.01460 (11)
Br2	0.01520 (14)	0.02324 (14)	0.01864 (14)	0.00351 (10)	0.00706 (10)	0.01260 (11)
N1	0.0155 (10)	0.0182 (10)	0.0157 (9)	0.0032 (8)	0.0068 (8)	0.0082 (8)
N2	0.0130 (10)	0.0168 (9)	0.0127 (9)	0.0020 (7)	0.0034 (8)	0.0074 (8)
N3	0.0114 (9)	0.0164 (10)	0.0144 (9)	0.0023 (7)	0.0043 (8)	0.0080 (8)
N4	0.0114 (9)	0.0153 (9)	0.0155 (9)	0.0029 (7)	0.0063 (8)	0.0070 (8)
C1	0.0155 (11)	0.0147 (11)	0.0154 (11)	0.0032 (9)	0.0051 (9)	0.0070 (9)
C2	0.0247 (14)	0.0188 (12)	0.0164 (11)	0.0058 (10)	0.0081 (10)	0.0073 (10)
C3	0.0241 (14)	0.0207 (12)	0.0127 (11)	0.0042 (10)	−0.0013 (10)	0.0051 (10)
C4	0.0154 (12)	0.0200 (12)	0.0207 (12)	0.0018 (9)	0.0018 (10)	0.0077 (10)
C5	0.0134 (11)	0.0195 (12)	0.0172 (11)	0.0015 (9)	0.0027 (9)	0.0080 (10)
C6	0.0140 (11)	0.0137 (10)	0.0118 (10)	0.0022 (8)	0.0023 (9)	0.0051 (9)
C7	0.0144 (11)	0.0180 (11)	0.0164 (11)	0.0028 (9)	0.0049 (9)	0.0092 (9)
C8	0.0138 (11)	0.0224 (12)	0.0121 (10)	0.0011 (9)	0.0037 (9)	0.0093 (9)
C9	0.0112 (11)	0.0190 (11)	0.0126 (10)	0.0015 (9)	0.0045 (9)	0.0077 (9)
C10	0.0169 (12)	0.0237 (12)	0.0200 (12)	0.0073 (10)	0.0079 (10)	0.0134 (10)
C11	0.0256 (14)	0.0194 (12)	0.0203 (12)	0.0074 (10)	0.0110 (11)	0.0098 (10)
C12	0.0208 (13)	0.0163 (11)	0.0157 (11)	0.0012 (9)	0.0063 (10)	0.0050 (9)
C13	0.0156 (12)	0.0204 (12)	0.0142 (11)	0.0028 (9)	0.0028 (9)	0.0076 (10)
C14	0.0125 (11)	0.0173 (11)	0.0126 (10)	0.0038 (9)	0.0044 (9)	0.0073 (9)
C15	0.0125 (11)	0.0171 (11)	0.0136 (11)	0.0019 (9)	0.0010 (9)	0.0062 (9)
C16	0.0138 (11)	0.0158 (11)	0.0149 (10)	0.0027 (9)	0.0057 (9)	0.0068 (9)
C17	0.0137 (11)	0.0123 (10)	0.0132 (10)	0.0019 (8)	0.0056 (9)	0.0040 (8)
C18	0.0143 (12)	0.0171 (11)	0.0178 (11)	0.0031 (9)	0.0068 (9)	0.0056 (9)
C19	0.0181 (12)	0.0166 (11)	0.0202 (12)	0.0017 (9)	0.0108 (10)	0.0056 (10)
C20	0.0229 (13)	0.0164 (11)	0.0167 (11)	0.0051 (9)	0.0104 (10)	0.0078 (9)
C21	0.0190 (12)	0.0165 (11)	0.0136 (11)	0.0061 (9)	0.0055 (9)	0.0075 (9)
C22	0.0139 (11)	0.0131 (10)	0.0135 (10)	0.0032 (8)	0.0068 (9)	0.0047 (9)
C23	0.0191 (12)	0.0223 (12)	0.0219 (12)	0.0056 (10)	0.0129 (10)	0.0113 (10)
C24	0.0286 (15)	0.0213 (12)	0.0278 (14)	0.0077 (11)	0.0175 (12)	0.0127 (11)
C25	0.0256 (14)	0.0196 (12)	0.0229 (13)	0.0050 (10)	0.0144 (11)	0.0103 (10)
C26	0.0257 (14)	0.0201 (12)	0.0219 (13)	0.0040 (10)	0.0130 (11)	0.0089 (10)
C27	0.0271 (14)	0.0201 (12)	0.0210 (12)	0.0032 (10)	0.0128 (11)	0.0078 (10)
C28	0.0225 (13)	0.0207 (12)	0.0177 (12)	0.0036 (10)	0.0085 (10)	0.0086 (10)
C29	0.0261 (14)	0.0243 (13)	0.0204 (12)	0.0028 (11)	0.0119 (11)	0.0095 (11)
C30	0.0219 (14)	0.0300 (14)	0.0252 (13)	0.0052 (11)	0.0102 (11)	0.0160 (12)
C31	0.0106 (11)	0.0194 (11)	0.0178 (11)	0.0044 (9)	0.0052 (9)	0.0078 (9)
C32	0.0134 (11)	0.0213 (12)	0.0188 (12)	0.0032 (9)	0.0049 (9)	0.0095 (10)
C33	0.0212 (13)	0.0232 (13)	0.0211 (12)	0.0013 (10)	0.0056 (10)	0.0115 (11)
C34	0.0183 (13)	0.0229 (13)	0.0231 (13)	0.0003 (10)	0.0068 (10)	0.0093 (11)
C35	0.0210 (13)	0.0214 (13)	0.0246 (13)	−0.0001 (10)	0.0090 (11)	0.0080 (11)
C36	0.0204 (13)	0.0223 (13)	0.0286 (14)	0.0033 (10)	0.0074 (11)	0.0119 (11)
C37	0.0259 (15)	0.0211 (13)	0.0260 (14)	0.0049 (11)	0.0061 (12)	0.0093 (11)
C38	0.0359 (18)	0.0339 (16)	0.0298 (15)	0.0072 (14)	0.0134 (13)	0.0148 (13)
O1W	0.0215 (11)	0.0275 (12)	0.0366 (13)	−0.0002 (9)	−0.0042 (9)	0.0141 (10)

N1—C7	1.338 (3)	C23—C24	1.519 (4)
N1—C1	1.390 (3)	C23—H23A	0.9900
N1—C23	1.476 (3)	C23—H23B	0.9900
N2—C7	1.337 (3)	C24—C25	1.525 (4)
N2—C6	1.395 (3)	C24—H24A	0.9900
N2—C8	1.482 (3)	C24—H24B	0.9900
N3—C16	1.334 (3)	C25—C26	1.518 (4)
N3—C17	1.395 (3)	C25—H25A	0.9900
N3—C15	1.469 (3)	C25—H25B	0.9900
N4—C16	1.331 (3)	C26—C27	1.518 (4)
N4—C22	1.395 (3)	C26—H26A	0.9900
N4—C31	1.477 (3)	C26—H26B	0.9900
C1—C2	1.393 (3)	C27—C28	1.527 (4)
C1—C6	1.394 (3)	C27—H27A	0.9900
C2—C3	1.387 (4)	C27—H27B	0.9900
C2—H2A	0.9500	C28—C29	1.522 (4)
C3—C4	1.406 (4)	C28—H28A	0.9900
C3—H3A	0.9500	C28—H28B	0.9900
C4—C5	1.380 (4)	C29—C30	1.528 (4)
C4—H4A	0.9500	C29—H29A	0.9900
C5—C6	1.397 (3)	C29—H29B	0.9900
C5—H5A	0.9500	C30—H30A	0.9800
C7—H7A	0.9500	C30—H30B	0.9800
C8—C9	1.508 (3)	C30—H30C	0.9800
C8—H8A	0.9900	C31—C32	1.523 (3)
C8—H8B	0.9900	C31—H31A	0.9900
C9—C10	1.402 (4)	C31—H31B	0.9900
C9—C14	1.407 (3)	C32—C33	1.527 (4)
C10—C11	1.386 (4)	C32—H32A	0.9900
C10—H10A	0.9500	C32—H32B	0.9900
C11—C12	1.383 (4)	C33—C34	1.532 (4)
C11—H11A	0.9500	C33—H33A	0.9900
C12—C13	1.400 (4)	C33—H33B	0.9900
C12—H12A	0.9500	C34—C35	1.519 (4)
C13—C14	1.396 (3)	C34—H34A	0.9900
C13—H13A	0.9500	C34—H34B	0.9900
C14—C15	1.520 (3)	C35—C36	1.531 (4)
C15—H15A	0.9900	C35—H35A	0.9900
C15—H15B	0.9900	C35—H35B	0.9900
C16—H16A	0.9500	C36—C37	1.529 (4)
C17—C18	1.393 (3)	C36—H36A	0.9900
C17—C22	1.397 (3)	C36—H36B	0.9900
C18—C19	1.389 (4)	C37—C38	1.515 (4)
C18—H18A	0.9500	C37—H37A	0.9900
C19—C20	1.405 (4)	C37—H37B	0.9900
C19—H19A	0.9500	C38—H38A	0.9800
C20—C21	1.387 (4)	C38—H38B	0.9800
C20—H20A	0.9500	C38—H38C	0.9800
C21—C22	1.403 (3)	O1W—H1W1	0.84 (5)
C21—H21A	0.9500	O1W—H2W1	0.83 (5)
C7—N1—C1	108.6 (2)	C23—C24—H24A	109.2
C7—N1—C23	126.4 (2)	C25—C24—H24A	109.2
C1—N1—C23	125.0 (2)	C23—C24—H24B	109.2
C7—N2—C6	108.2 (2)	C25—C24—H24B	109.2
C7—N2—C8	128.7 (2)	H24A—C24—H24B	107.9
C6—N2—C8	122.9 (2)	C26—C25—C24	113.0 (2)
C16—N3—C17	108.5 (2)	C26—C25—H25A	109.0
C16—N3—C15	125.8 (2)	C24—C25—H25A	109.0
C17—N3—C15	125.6 (2)	C26—C25—H25B	109.0
C16—N4—C22	108.3 (2)	C24—C25—H25B	109.0
C16—N4—C31	126.3 (2)	H25A—C25—H25B	107.8
C22—N4—C31	125.4 (2)	C27—C26—C25	113.4 (2)
N1—C1—C2	131.5 (2)	C27—C26—H26A	108.9
N1—C1—C6	106.4 (2)	C25—C26—H26A	108.9
C2—C1—C6	122.1 (2)	C27—C26—H26B	108.9
C3—C2—C1	115.6 (2)	C25—C26—H26B	108.9
C3—C2—H2A	122.2	H26A—C26—H26B	107.7
C1—C2—H2A	122.2	C26—C27—C28	113.4 (2)
C2—C3—C4	122.4 (2)	C26—C27—H27A	108.9
C2—C3—H3A	118.8	C28—C27—H27A	108.9
C4—C3—H3A	118.8	C26—C27—H27B	108.9
C5—C4—C3	121.7 (3)	C28—C27—H27B	108.9
C5—C4—H4A	119.2	H27A—C27—H27B	107.7
C3—C4—H4A	119.2	C29—C28—C27	114.5 (2)
C4—C5—C6	116.2 (2)	C29—C28—H28A	108.6
C4—C5—H5A	121.9	C27—C28—H28A	108.6
C6—C5—H5A	121.9	C29—C28—H28B	108.6
C1—C6—N2	106.8 (2)	C27—C28—H28B	108.6
C1—C6—C5	122.0 (2)	H28A—C28—H28B	107.6
N2—C6—C5	131.1 (2)	C28—C29—C30	112.1 (2)
N2—C7—N1	110.0 (2)	C28—C29—H29A	109.2
N2—C7—H7A	125.0	C30—C29—H29A	109.2
N1—C7—H7A	125.0	C28—C29—H29B	109.2
N2—C8—C9	113.9 (2)	C30—C29—H29B	109.2
N2—C8—H8A	108.8	H29A—C29—H29B	107.9
C9—C8—H8A	108.8	C29—C30—H30A	109.5
N2—C8—H8B	108.8	C29—C30—H30B	109.5
C9—C8—H8B	108.8	H30A—C30—H30B	109.5
H8A—C8—H8B	107.7	C29—C30—H30C	109.5
C10—C9—C14	119.5 (2)	H30A—C30—H30C	109.5
C10—C9—C8	117.3 (2)	H30B—C30—H30C	109.5
C14—C9—C8	123.1 (2)	N4—C31—C32	112.6 (2)
C11—C10—C9	120.8 (2)	N4—C31—H31A	109.1
C11—C10—H10A	119.6	C32—C31—H31A	109.1
C9—C10—H10A	119.6	N4—C31—H31B	109.1
C12—C11—C10	119.9 (2)	C32—C31—H31B	109.1
C12—C11—H11A	120.0	H31A—C31—H31B	107.8
C10—C11—H11A	120.0	C31—C32—C33	113.9 (2)
C11—C12—C13	120.0 (2)	C31—C32—H32A	108.8
C11—C12—H12A	120.0	C33—C32—H32A	108.8
C13—C12—H12A	120.0	C31—C32—H32B	108.8
C14—C13—C12	120.7 (2)	C33—C32—H32B	108.8
C14—C13—H13A	119.6	H32A—C32—H32B	107.7
C12—C13—H13A	119.6	C32—C33—C34	113.6 (2)
C13—C14—C9	119.0 (2)	C32—C33—H33A	108.9
C13—C14—C15	121.2 (2)	C34—C33—H33A	108.9
C9—C14—C15	119.7 (2)	C32—C33—H33B	108.9
N3—C15—C14	113.37 (19)	C34—C33—H33B	108.9
N3—C15—H15A	108.9	H33A—C33—H33B	107.7
C14—C15—H15A	108.9	C35—C34—C33	113.3 (2)
N3—C15—H15B	108.9	C35—C34—H34A	108.9
C14—C15—H15B	108.9	C33—C34—H34A	108.9
H15A—C15—H15B	107.7	C35—C34—H34B	108.9
N4—C16—N3	110.3 (2)	C33—C34—H34B	108.9
N4—C16—H16A	124.9	H34A—C34—H34B	107.7
N3—C16—H16A	124.9	C34—C35—C36	113.6 (2)
C18—C17—N3	131.4 (2)	C34—C35—H35A	108.8
C18—C17—C22	122.3 (2)	C36—C35—H35A	108.8
N3—C17—C22	106.2 (2)	C34—C35—H35B	108.8
C19—C18—C17	115.9 (2)	C36—C35—H35B	108.8
C19—C18—H18A	122.0	H35A—C35—H35B	107.7
C17—C18—H18A	122.0	C37—C36—C35	113.8 (2)
C18—C19—C20	122.0 (2)	C37—C36—H36A	108.8
C18—C19—H19A	119.0	C35—C36—H36A	108.8
C20—C19—H19A	119.0	C37—C36—H36B	108.8
C21—C20—C19	122.3 (2)	C35—C36—H36B	108.8
C21—C20—H20A	118.9	H36A—C36—H36B	107.7
C19—C20—H20A	118.9	C38—C37—C36	114.1 (3)
C20—C21—C22	115.7 (2)	C38—C37—H37A	108.7
C20—C21—H21A	122.1	C36—C37—H37A	108.7
C22—C21—H21A	122.1	C38—C37—H37B	108.7
N4—C22—C17	106.7 (2)	C36—C37—H37B	108.7
N4—C22—C21	131.4 (2)	H37A—C37—H37B	107.6
C17—C22—C21	121.8 (2)	C37—C38—H38A	109.5
N1—C23—C24	112.5 (2)	C37—C38—H38B	109.5
N1—C23—H23A	109.1	H38A—C38—H38B	109.5
C24—C23—H23A	109.1	C37—C38—H38C	109.5
N1—C23—H23B	109.1	H38A—C38—H38C	109.5
C24—C23—H23B	109.1	H38B—C38—H38C	109.5
H23A—C23—H23B	107.8	H1W1—O1W—H2W1	108 (4)
C23—C24—C25	112.0 (2)
C7—N1—C1—C2	−177.9 (3)	C9—C14—C15—N3	165.0 (2)
C23—N1—C1—C2	2.6 (4)	C22—N4—C16—N3	−0.3 (3)
C7—N1—C1—C6	0.7 (3)	C31—N4—C16—N3	−177.1 (2)
C23—N1—C1—C6	−178.8 (2)	C17—N3—C16—N4	0.4 (3)
N1—C1—C2—C3	178.2 (3)	C15—N3—C16—N4	177.2 (2)
C6—C1—C2—C3	−0.2 (4)	C16—N3—C17—C18	176.6 (3)
C1—C2—C3—C4	0.2 (4)	C15—N3—C17—C18	−0.3 (4)
C2—C3—C4—C5	0.1 (4)	C16—N3—C17—C22	−0.3 (3)
C3—C4—C5—C6	−0.5 (4)	C15—N3—C17—C22	−177.2 (2)
N1—C1—C6—N2	−0.9 (3)	N3—C17—C18—C19	−176.5 (2)
C2—C1—C6—N2	177.9 (2)	C22—C17—C18—C19	0.0 (4)
N1—C1—C6—C5	−178.9 (2)	C17—C18—C19—C20	−0.1 (4)
C2—C1—C6—C5	−0.1 (4)	C18—C19—C20—C21	0.2 (4)
C7—N2—C6—C1	0.8 (3)	C19—C20—C21—C22	−0.1 (4)
C8—N2—C6—C1	175.7 (2)	C16—N4—C22—C17	0.1 (3)
C7—N2—C6—C5	178.5 (3)	C31—N4—C22—C17	177.0 (2)
C8—N2—C6—C5	−6.5 (4)	C16—N4—C22—C21	−176.8 (2)
C4—C5—C6—C1	0.5 (4)	C31—N4—C22—C21	0.0 (4)
C4—C5—C6—N2	−177.0 (2)	C18—C17—C22—N4	−177.1 (2)
C6—N2—C7—N1	−0.3 (3)	N3—C17—C22—N4	0.1 (3)
C8—N2—C7—N1	−174.9 (2)	C18—C17—C22—C21	0.2 (4)
C1—N1—C7—N2	−0.3 (3)	N3—C17—C22—C21	177.4 (2)
C23—N1—C7—N2	179.2 (2)	C20—C21—C22—N4	176.5 (2)
C7—N2—C8—C9	−29.6 (4)	C20—C21—C22—C17	−0.1 (3)
C6—N2—C8—C9	156.5 (2)	C7—N1—C23—C24	101.5 (3)
N2—C8—C9—C10	−94.4 (3)	C1—N1—C23—C24	−79.1 (3)
N2—C8—C9—C14	89.2 (3)	N1—C23—C24—C25	165.2 (2)
C14—C9—C10—C11	−0.9 (4)	C23—C24—C25—C26	170.9 (2)
C8—C9—C10—C11	−177.4 (2)	C24—C25—C26—C27	170.5 (3)
C9—C10—C11—C12	0.0 (4)	C25—C26—C27—C28	173.2 (2)
C10—C11—C12—C13	0.4 (4)	C26—C27—C28—C29	170.3 (2)
C11—C12—C13—C14	0.1 (4)	C27—C28—C29—C30	−176.1 (2)
C12—C13—C14—C9	−0.9 (4)	C16—N4—C31—C32	−98.8 (3)
C12—C13—C14—C15	−179.4 (2)	C22—N4—C31—C32	84.9 (3)
C10—C9—C14—C13	1.4 (4)	N4—C31—C32—C33	73.6 (3)
C8—C9—C14—C13	177.6 (2)	C31—C32—C33—C34	174.3 (2)
C10—C9—C14—C15	179.9 (2)	C32—C33—C34—C35	66.7 (3)
C8—C9—C14—C15	−3.8 (4)	C33—C34—C35—C36	176.1 (2)
C16—N3—C15—C14	102.7 (3)	C34—C35—C36—C37	−173.0 (2)
C17—N3—C15—C14	−80.9 (3)	C35—C36—C37—C38	−59.2 (4)
C13—C14—C15—N3	−16.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···Br1	0.83 (5)	2.50 (5)	3.326 (3)	173 (4)
O1W—H2W1···Br2	0.83 (5)	2.52 (5)	3.343 (3)	177 (5)
C7—H7A···Br1	0.95	2.69	3.569 (3)	154
C15—H15A···Br1	0.99	2.92	3.672 (3)	134
C16—H16A···Br1	0.95	2.79	3.594 (3)	143
C2—H2A···Br2i	0.95	2.81	3.698 (3)	155
C4—H4A···O1Wii	0.95	2.49	3.218 (4)	133
C8—H8A···Br1iii	0.99	2.80	3.779 (3)	169
C8—H8B···Br2iii	0.99	2.71	3.655 (3)	159
C19—H19A···Br2iv	0.95	2.84	3.770 (3)	167
C21—H21A···Br2v	0.95	2.90	3.785 (3)	155
C31—H31A···Br2v	0.99	2.87	3.786 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯Br1	0.83 (5)	2.50 (5)	3.326 (3)	173 (4)
O1W—H2W1⋯Br2	0.83 (5)	2.52 (5)	3.343 (3)	177 (5)
C7—H7A⋯Br1	0.95	2.69	3.569 (3)	154
C15—H15A⋯Br1	0.99	2.92	3.672 (3)	134
C16—H16A⋯Br1	0.95	2.79	3.594 (3)	143
C2—H2A⋯Br2i	0.95	2.81	3.698 (3)	155
C4—H4A⋯O1Wii	0.95	2.49	3.218 (4)	133
C8—H8A⋯Br1iii	0.99	2.80	3.779 (3)	169
C8—H8B⋯Br2iii	0.99	2.71	3.655 (3)	159
C19—H19A⋯Br2iv	0.95	2.84	3.770 (3)	167
C21—H21A⋯Br2v	0.95	2.90	3.785 (3)	155
C31—H31A⋯Br2v	0.99	2.87	3.786 (3)	154

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .